Chloromethyl Methyl Ether → 1-(Methoxymethoxy)-3-propylbenzene

HRID 2035411Notes

Reaction equation

HRID 2035411 reaction equation
[CH3:1][O:2][CH2:3]Cl.C(=O)([O-])[O-].[K+].[K+].[CH2:11]([C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1)[CH2:12][CH3:13]>CN(C)C=O>[CH3:1][O:2][CH2:3][O:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH2:11][CH2:12][CH3:13])[CH:15]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 693023-Propylphenol

Product 1

HCID 224937211-(Methoxymethoxy)-3-propylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methoxymethyl chloride (8.4 mL) and potassium carbonate (30 g) were added to an N,N-dimethylformamide (150 mL) solution of 3-propylphenol (10 g) at room temperature, followed by stirring at 50° C. for one day. The reaction solution was poured into ice water. The insoluble matter was filtered off, and extracted with a hexane-ethyl acetate (1:1) mixed solvent. The organic layer was successively washed with water and brine. The resultant was dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane only to hexane:ethyl acetate=10:1), to thereby obtain the title compound (8.0 g) having the following physical properties.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. extractionextracted with a hexane-ethyl acetate (1:1)
  3. additionmixed solvent
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialThe resultant was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane only to hexane

Sources & evidence

ORD record
ord-a09bca3b10f2447e8dc913799fffe341
Source dataset
uspto-grants-2013_11
Patent number
US08575134B2

Reaction notes

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